


Tempest Rising

by JackBivouac



Series: Skull and Shackles [3]
Category: Dungeons & Dragons (Roleplaying Game), Original Work, Pathfinder (Roleplaying Game)
Genre: Bondage, Bukkake, Chair Bondage, Dildos, Double Penetration, F/M, Forced Orgasm, Interspecies Sex, M/M, Multi, Other, Pirates, Public Humiliation, Public Sex, Rape, Sea Monsters, Size Difference, Tentacle Rape
Language: English
Status: Completed
Published: 2019-09-01
Updated: 2019-09-22
Packaged: 2020-10-04 09:47:44
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Rape/Non-Con
Chapters: 4
Words: 3,806
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20469023
Author URL: https://archiveofourown.org/users/JackBivouac/pseuds/JackBivouac
Summary: New backstory oneshots in Tempest Academy, pirate guildhouse, deviating/derived from a Skull and Shackles campaign





	1. Join the Pirate's Guild, They Said

The Isles of the Shackles took all who came to their pirate-ruled wilds, but those who wished to join the Free Captains of the Fever Sea first had to submit to an education at one of the many pirate guildhouses. In Port Peril, aspirants young and old flocked to Tempest Academy to attend the local guild’s entrance exam.

The aspirants were split into four groups for testing. Secho, a Mwangi native of the Shackles, was put into Group A. He was a youth of middling height and slight but wiry build with dark brown skin and a short ponytail of dreadlocks. He followed Group A out from Tempest Academy to the docks of Port Peril where a large crowd had already gathered despite the early hour.

The proctor, a hulking, black-bearded half-orc, stood on a wooden platform occupied by a row of stocks, just enough to hold each member of Group A. He smirked at the aspirants, which did nothing to quell their mounting unease.

“What sets a Free Captain apart from a mere pirate is the code of the Shackles, the laws of domination and submission. If you wish to dominate, you must first learn to submit.”

The crowd let out a sinister cheer. Already, a few of the aspirants began to back out from the group. Secho, however, set his jaw and stood his ground. 

The Free Captains were the only organization in all of the Shackles that fought back the tide of the infernal Chelaxian Navy. If he wished to use them, it was only natural that he would be used as well.

“Cast down your weapons and strip. The stocks of fate await you,” said the half-orc. 

His merciless laugh was echoed a hundred times over by the crowd. Secho ignored the Group A deserters and the jeering audience. He climbed naked onto the platform along with the handful of remaining aspirants and placed his arms and neck into an open pillory.

The proctor walked down the line of aspirants, closing and locking their stocks with a heavy, final clunk. “You are free to bail at any time, but in doing so you negate your eligibility to join any of our illustrious guilds for the rest of the year. Those who wish to pass the exam must submit to the whims of the crowd until sundown. Are there any questions?”

There were not, although a third of the remaining aspirants decided to bail before the testing had even begun.

“Excellent. Then let the testing begin.”

#*#*#*#*

Group B was taken past the stocks on their way to the docks as well. The humiliation suffered by Group A was enough to freeze half the aspirants in their tracks.

Strangers from the crowd swarmed the naked, restrained hopefuls from all sides. Dicks were thrust into their mouths, ears, hands, pussies, and anuses, ripping their walls apart. Cunts and cocks were braced against their legs and other flesh to grind.

The grunting, choking, sobbing members of Group A were completely covered in cum, those of strangers and some of their own. 

Secho, true to his wish, allowed his body to succumb to the rape like any mounted animal bitch. His body spasmed between the unyielding wood of the stocks and the violent piston of two dicks in his anus, his shaft squeezing shut and wringing the penetrants of their seed. He was one of the few who moaned around the dick stuffing his throat.

A tall, unnaturally pale refugee of distant Korvosa followed Group B’s proctor without a single glance at the stocks. His or their pin-straight, platinum hair fell past his shoulders like a short cloak. Sieben stopped with his vastly diminished group on the deck of a two-masted brig.

“Your test,” said the proctor, a native Mwangi woman, “is to climb to the top of the foremast and unfurl and set the sail from the top yard. Before one of my crew does the same on the mizzenmast.”

Sieben’s piercing blue eyes narrowed at the yard. The sail was tied at four locations. Untying all of one side, however, would cause the sailcloth to flap around the breeze and ultimately make it more difficult to secure.

“Who’s up first?”

The palest of the aspirants raised a slender hand.

The proctor’s crewmember laughed derisively but smacked Sieben on the shoulder. “I like your guts, ya fish-pale landlubber. Gonna enjoy ‘em even more when they’re being swabbed off the deck.”

Sieben said nothing, merely giving the shorter human a thin, tilted smile. Far too thin to reveal the pointed tips of the dhampir’s fangs. He walked to the base of the foremast, forcing the pirate to head off to their own.

“On my mark...GO!”

The remainder of Group B fell into stunned silence. The fish-pale landlubber scaled his mast as nimbly as a ship’s rat. He was halfway to the yard by the time his opponent had climbed up a third. Group B broke into wild cheers.

None of them noticed the other member of the proctor’s crew padding quietly across the deck. The ratfolk leaned against the rows of hooked ropes to the foremast. They just so happened to hold a dagger in one paw. Which just so happened to saw through the line securing the forestay boom.

Whoosh! The boom swung free. Sieben had only enough time to catch the movement in the corner of his eye. The boom crashed into the foremast rigging, shaking him off the yard.

Sieben fell, flailing for any hold. Fingers slipped against wood. He snarled and grasped for the rigging. The coarse rope burned the skin of his fist, but he jerked to a stop, feet dangling over thirty feet over the deck.

It was a nasty trick, but one the pirates couldn’t try again. That made all the difference.

The dhampir swung his other hand onto the rigging, bracing. With inhuman strength, he launched himself ten feet back up to the yard. Group B roared out their cheers.

The unfurled, secured topsail swelled out before him. Sieben finally allowed himself a wider smile even more askew than the first. 

He would bide his time here in the Shackles, learn every trick these cutthroats had to offer. When he finally returned to Korvosa, he would return with a vengeance.


	2. It'll Be Fun, They Said

Group C was taken inside the Tempest Academy proper and were greeted with warm, rowdy clangor even at this morning hour. The vast, soaring entryway served as a massive tavern and gambling hall to Free Captains, their crew, and any other patron unaffiliated with the colonizers of the Infernal Empire of Cheliax.

Scantily clad servers split up the group, beckoning each member to a different gambling table. Akht, a bronze-skinned Osirian with thick, dark brown hair cut just above their shoulders eyed the chair pulled out by the server with mounting apprehension.

The heavy wooden chair’s seat had been modified so that two thick, wooden dildoes stood there erect. Iron cuffs gaped open and waiting for their ankles from the legs of the chair. Thick leather straps hung from its back.

Akht looked from the viciously grinning gamblers at the table to the welcoming but unreassuring smile of the server. They had just escaped from a life of slavery logging timber from the Shackles mainland. But with nothing to return to, they could only move forward into these new, temporary bonds.

The runaway moved to take a ginger seat, but the server caught them by the sleeve.

“Forgive me, I forgot to mention, but this exam must be conducted entirely in the nude.”

The gamblers chuckled darkly over their cards, leering at Akht in anticipation. The runaway swallowed hard but gave the server a stiff nod. They shut all thought from their mind and removed their rags as swiftly as possible, but shame still burned hot from their chest and up their slender neck to darken their lips and cheeks.

With every generous whipscar and curve bared, Akht finally took a seat, stifling their grunt as they eased the mouths of their pussy and asshole over the dildoes. The wood was even thicker and more solid than it looked, splitting their walls painfully wide and crushing the thin, shared flesh between pussy and anus.

Akht broke into a sweat before the dildoes had even penetrated them to the hilt. The server pushed down on their shoulders to finish the job. A high-pitched squeal escaped the runaway, the dildoes ramming against their womb and anal g-spot.

The gamblers roared with jeering laughter. Before Akht had time to adjust to their overstuffed shafts, the server belted them above and below the tits to the back of the chair and snapped the cuffs shut around their ankles.

“Remember, you can bail at any time,” the server reminded ‘helpfully.’ They placed a handful of cards into Akht’s sweaty hands. Then strapped their wrists together over their lap. “But if you wish to pass, you have to play ten rounds of Bastard’s Fool.”

Akht nodded vehemently, not trusting themself to speak.

“Then let the games begin!” the server announced, their smile unchanged.

As the gamblers pushed forward their initial bets, the dildoes penetrating the full length and squeeze of Akht’s shafts pistoned to life. The runaway jumped against their bonds with an ungainly squawk, nearly scattering their stack of chips all across the table.

The pirates laughed and jeered, slapping each other at Akht’s poorly controlled whimpers and writhing. Those on either side of the Osirian groped the soft, round flesh of their breasts, tweezing their nipples, or twisted and teased their clit and cunt.

Akht, utterly defenseless to the assaulting hands and dildoes churning their pussy and anus to a wet, spasming pulp, had no focus to spare. It took every ounce of their willpower to play their cards. They couldn’t stop their tongue lolling from their mouth or the sharp gasps from the dildoes pounding their guts.

“C-c-call!” Akht shrieked, their back arching against the chair. Convulsions battered their wracking body against the wood. They drooled helplessly into their lap, sticky drops splattering their cards.

“Congratulations,” chirped the server. “You’ve won the first round. Only nine more to go!”

#*#*#*#*

Group D was taken from Tempest Academy’s gambling hall down the stairs to the basement. A large fighting ring had been set up at the center of the room, surrounded by a huge crowd that whipped up into a whooping frenzy at the sight of the aspirants. They jostled each other out of the way for the proctor, an immigrant from godless Rahadoum, to lead the group to the ropes of the ring.

“Out at sea, you must be prepared to face your opponents at all kinds of disadvantages. Here, we’ll keep it simple. You’ve been captured and taken aboard an enemy vessel, Chelish navy, no doubt. Your goal is not to be thrown ‘overboard’ so that you can live to take your vengeance. Reasonable, no?”

Nenu, a Tian-Min with long black hair in the hime cut that was all the rage in the distant city of Kasai this year, could only shrug and nod. She was all about survival these days, thanks and no thanks to her scheming branch family.

“Those who agree, put your hands behind your back.”

Group D split asunder at that. Nenu stepped into the front line with those who agreed. The proctor snapped shackles joined by a single link tight around either wrist, restraining her hands and arms tight behind her back.

The ground quaked underfoot as one very large, very dangerous opponent jumped down into the ring. The marsh giant, more wall of solid, green-skinned flesh than humanoid rose to his full eleven-foot stature and let out a skull-ringing roar. The swamp dweller weighed nearly two thousand pounds, easily more than the combined weights of the aspirants who did not draw back at sight of their would-be opponent.

The proctor laughed with the spectators. She raised the ropes of the ring to create an opening. “Those who still wish to test may enter.”

Nobody moved. Nenu grit her teeth. The marsh giant was as close to an oni as she would likely encounter out here. She would have to face them one day. It might as well be today.

Nenu ran into the ring. And immediately tripped over the bottom rope. She fell onto her face, breasts and knees with her ass up in the air. It was not a fighting stance but a submissive one, which was the only reason the marsh giant did not immediately toss her shackle-bound body out of the ring.

Instead, he lumbered over as she tried to gain her bearings over the spinning in her head. Before she could rise or even roll onto her side, he scooped her up by the belly in one hand and ripped the trousers and panties off the smooth curve of her ass.

“Fuck you!” Nenu shouted in noble outrage, kicking her heels out behind her. She might as well have been kicking a wall of stone.

The giant closed his fist around her waist. Her eyes bulged as the air squeezed from her lungs. He hefted her up, setting the tiny hole of her anus atop the thick, heated mass of his cock. He shoved the Minkaian girl down the full length of his dick.

Nenu’s mouth opened in a soundless scream, saliva splattering onto the fighting ring floor. The giant pumped her entire body up and down his cock like fleshy fucksock, his massive dick tearing her anal walls apart.

Nenu’s legs continued to kick, though no longer under her own control. Every piston into her asshole rammed the giant’s dick into her guts. White hot pain and pleasure exploded through her fist-constricted body, sending her twitching and jerking in unstoppable convulsions in the giant’s grasp.

Despite her agonized writhing, she was not cast out of the ring. The tight suck of her anus around the giant’s massive, raping cock made sure of it. Reassured, other shackled aspirants of Group D entered the ring.

Cum exploded into Nenu’s asshole, swelling her belly with its sheer volume. The giant’s seed untethered the last of her tortured, fleeting consciousness. He dropped her to the floor of the ring, leaking sticky white between her legs. As her world faded into darkness, he picked up the next of the would-be pirates.


	3. Sunken Booty

As brand spanking new members of Tempest Academy, those who passed the entrance exam were not given their own pirating vessel. They were assigned to vessels of those who’d recently made the rank of captain. Secho, Sieben, Akht, and Nenu were all placed aboard the Shining Star under the command of Captain Vakar, a lanky, golden-eyed half-orc evoker whose monkey familiar, Mister Swabb, was never far behind.

The Shining Star immediately set a course for the wreck of what the guild believed to be the Brine Banshee, a pirate vessel notorious for preying upon Free Captains. 

Tempest Academy had received word that a ship of its like had been spotted fleeing pursuit along the fringe of the Eye of Abendego, the vicious, permanent hurricane off Garund’s western coast. The ship steered too close to the supernatural maelstrom and was struck down by wind and lightning. The vessel was rent asunder, the smaller bow section sinking to a stop in relatively shallow waters but the larger bow section dropping into an underwater trench. Magic, therefore, was the only means of confirming the Brine Banshee’s wreck and otherwise looting the vessel.

Captain Vakar set anchor off the coast rather than the Eye. She cast water breathing and endure elements on herself and the crew, including the four new guildmembers. 

“Nobody gets back on board without treasure,” she winked, “so let’s get diving!”

She jumped into the water with a whoop, followed by the cheers and splashes of her crew. Only Secho, Sieben, Akht, and Nenu remained behind.

Secho sat on the ship’s rail with his back to the waters. He shot his fellow newbs a wide, nervous grin. “Bottoms up.”

He tipped back over the rail, hitting the water with a warm, stinging smack. About half the crew was already combing over the bow sixty feet below. He could confirm just from here that this was definitely the Brine Banshee. And that there’d be nothing left to find there.

Sieben, Akht, and Nenu dropped in behind/above him. Secho pointed toward the dark, jagged mouth of the rift. They could do what they liked, but he was heading down with the captain and the other half of the crew.

The three new members nodded and followed him into the deep water. It was cold here, the temperature dropping as they made their slow descent. The water closed around them in layer after heavy layer, making it difficult to breath even with the captain’s magic.

Nearly two hundred feet from the surface, a hand grasped Secho’s shoulder. The boy nearly jumped out of his skin. But it was only Sieben. With his darkvision, the dhampir had seen something Secho could not. The boy let him take the lead.

The wreck of the stern drifted into gloomy view. There was a gentle, swaying movement from the helm. A moldering corpse was lashed to the ship’s wheel. Bones and partial humanoid skeletons littered the gun deck. Equally pallid crustaceans clung to the ship’s timbers around a gaping hole.

Secho’s eyes narrowed not to improve his sight but in suspicion. Not a single member of the Shining Star had been stationed outside the hole as a watch. He followed Sieben into the deeper darkness with his senses on high alert.

The floor of the cargo hold was littered with broken timber and smashed crates. Clusters of barnacles and slime growths infested the walls and every other viable surface. There was still no sign of the crew, but there at the back of the hold a familiar shape floated upright in the darkness.

Captain Vakar turned around. Her face was oddly slack, expressionless. Especially given the unsheathed cutlass grasped in her hand.

‘Captain?’ Secho mouthed, his eyes searching the darkness for the suspiciously absent Mister Swabb.

Instead of a monkey, however, he caught sight of a very, very long tentacle. Secho jerked back toward the others. All three were staring slack-jawed in front of them. He squinted over his shoulder, shaking Sieben all the while.

A school of pale, shimmering fish swirled between them and the captain in hypnotic formations. Literally.

Secho pried his eyes away. He tried shaking Akht. Nenu. They were all captivated. From the bottom corner of his eye, he watched, horrified, as an illusory wall peeled away from under them, revealing the unmoving bodies of the crew beneath their feet.

A heavy, slimy tentacle closed around his throat. Secho’s hands instinctively clawed at his assailant. Just as a second tentacle lashed tight down the length of his upper arms and chest, pinioning them to his body.

Secho’s lower arms flailed uselessly under the tentacle’s coils, his legs kicking madly. A third and final tentacle squeezed under his belt and between his thrashing legs. He screamed a cone of bubbles as the tentacle’s thick, fisted head shoved up his asshole.

The massive dick-tentacle ripped through Secho’s anal walls, pounding his g-spot into his guts. His eyes bulged, his stomach clenching at the pistoning blows, as did the shaft of his ass.

Secho doubled over, screaming bubbles. His anus only clamped ever tighter around the slimy, weighty tentacle railing his g-spot. It was more than the poor boy could take. His eyes rolled to the back of his head, a cloud of cum bursting into the water from his forcibly hardened dick.

The tatters of consciousness fluttered in the heat of his climax. The dick-tentacle continued uncaring, the binding tentacles aiding to shove his heated body up and down the cock’s length like a fleshy sock. Inhuman seed exploded into his ass, tearing away the last shreds of his consciousness.

Secho slipped into watery darkness, the cum of his unseen rapist flooding his deepest cavity.


	4. Cocoon of the Sea

Secho’s eyes opened to a world of blue. Blue light in the water. He was floating...underwater?

Memories of the sunken ship, the tentacles, flooded back. He swam up with a panicked gasp of bubbles. He broke through the invisible liquid layer over top of his glass tank.

He was no longer in the wreck but a vast chamber whose stone walls were lined with strange, glowing machinery and tubes. The entire chamber was flooded, the water mixed with a viscous, transparent slime. He knew because he’d inhaled a mouth full of it.

Secho sputtered and choked on the slimy water, but his lungs didn’t have a trace of that tell-tale burn of suffocation. He could breathe underwater.

He calmed in its cool, slightly swaying drift. His tank wasn’t the only one in the room. Sieben, Akht, and Nenu floated unconscious in cylindrical tanks of their own. One by one, Secho hauled them out into the free-flowing water.

Their eyes fluttered open. After gasping down a few slimy first breaths, they steadied enough to help Secho search the flooded laboratory for others and any clues of its owner.

The currents in the water shifted gently to flow past their ears. They carried with them a voice that resonated deep within their cores.

‘If you’re looking for your captain, I hate to be the bearer of bad news, but she didn’t survive the slave transformation. Neither did her little monkey.’

‘Slave transformation?’

‘Why do you think you can suddenly breathe underwater?’ 

As the voice spoke, three, now four tentacles undulated out from behind an illusory wall, seemingly out from the deep blue itself. They were followed by three red, glowing eyes on the head of a primeval, fishlike creature stretching twenty-five feet from head to tail.

‘Now, you’re mine!’ Lashing black tentacles erupted from every floor and wall.

It should’ve spelled the end of freedom from Secho and his companions, but they slipped through the water as fast as fish, darting through and between the coiling tentacles.

‘Get back here!’ the aboleth roared into their minds, their words charged with psychic magic.

Nenu slowed, looking back. Black tentacles seized around her arms and legs.

Secho and Sieben grabbed her under either arm. Not today. The layer of water against their skin turned slick as grease. Together, they yanked Nenu free.

The aboleth’s tentacles surged after them. Akht, a wickedly sharp sickle in either hand, hooked a tentacle in each. They slashed their catch to bloody stumps.

The aboleth’s psychic scream burst through their skulls, the creature churning the bloody waters with their writhing. Unable to concentrate through the pain, the black tentacles shuddered and vanished.

The door was clear. Secho, Sieben, Akht, and Nenu swam out from the laboratory. This time, they didn’t look back.


End file.
